


Sequel

by Taciturn



Series: Obey Me! Shenanigans [13]
Category: Shall We Date?: Obey Me!
Genre: Anal, Dom/sub Undertones, F/M, Face-Sitting, Multi, Multiple Orgasms, Orgasm Delay/Denial, Pet Play, Plot What Plot/Porn Without Plot, Sex Toys, Size Kink, Smut, Threesome - F/M/M, Unedited bc yolo
Language: English
Status: Completed
Published: 2021-02-27
Updated: 2021-02-27
Packaged: 2021-03-18 12:13:20
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,412
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29733702
Author URL: https://archiveofourown.org/users/Taciturn/pseuds/Taciturn
Summary: A follow up to Press PlaySimeon hatches a plan to include Diavolo in his next feature film.
Relationships: Diavolo (Shall We Date?: Obey Me!)/Reader, Diavolo/Simeon (Shall We Date?: Obey Me!)/Reader, Simeon (Shall We Date?: Obey Me!)/Reader, Simeon/Diavolo/Reader
Series: Obey Me! Shenanigans [13]
Series URL: https://archiveofourown.org/series/1837717
Comments: 4
Kudos: 73





	Sequel

**Author's Note:**

> There was a comment on Press Play about showing Diavolo the tape Simeon and Lucifer made with you. Things spiraled down from there. Y'all know what kind of trash I'm all about being.

There was a certain tension in the air you couldn't quite place. The pointed glances Diavolo made over his cup made you uneasy. It was made worse with how Simeon seemed blissfully unaware of just how heated the Demon Lord's gaze was whenever he glanced at the angel. You felt out of place, to say the least; but there was no getting out of a personal invitation to tea from Diavolo.    
  
"I do hope classes are going well for you." Diavolo broke the silence with mundane chit chat, though there was still the underlying feeling that he was hiding his true feelings from you. "Have you found things to do to alleviate your stress?" 

Before you could speak, Simeon answered for you, his tone matched Diavolo's; chipper yet oddly restrained. "Oh yes, we've gotten into the habit of meeting up to go through a movie on Lucifer's watch list. It's quite extensive. Everyone benefits from a little stress relief at the end of the week, don't you think?" Diavolo laughed jovially, his expression no longer as tense when Simeon explained your weekly "relaxation" activities.    
  
"Oh absolutely!" Diavolo agreed. "Nothing like a good movie and some quality time with friends!" You heard his voice lilt just slightly at the end, an oddly fragile note to his overall happy-go-lucky attitude. Was that a… pout you saw forming at the corner of his mouth? 

Simeon chuckled, taking a small sip of his tea, ignoring whatever signs the demon lord might have been dropping. “Yes, the quality of time spent with my dear friends has been nothing short of exquisite. It is such a shame that Lucifer is away on business this week and we will have to skip out on our regular meetup. I was so looking forward to the film this week too.” 

“Oh, what was on the watch list this week?” Diavolo’s eyes lit up in excitement. “Was it something I’ve seen before?” 

“Ah, we were… going to view a film we shot together.” Simeon’s smile was ironically innocent for what he had just said. The silence that followed from his statement said volumes and only added to the tension in the room. 

“ _ Oh. _ ” Diavolo finally stuttered, blushing madly. “Lucifer has advised me of your ah… filmmaking endeavors, I hear you’re quite the director.”    
  
It was your turn to blush. Diavolo  _ knew _ of what you did with Simeon and Lucifer. Lucifer  _ told _ him about the film you had made. Even if it hadn’t been said out loud, you had thought the recording would have been a secret between the three of you. “Well. I uh... “ You stammered, trying to come up for a defense for yourself. 

“Well, since you’ve already screened my latest work, what are your thoughts?” Simeon cut you off. The look in his eyes had changed, there was a glint of mischief and the heat in them matched Diavolo’s. “I’m always open for constructive criticism.”    
  
Diavolo looked to the side, to the ceiling, to the carpet below, anywhere but right in front of him where Simeon sat. He cleared his throat and loosened the collar on his top. “Well. If uh.. I had a say in it, I think I’d like to perhaps partake in the sequel you had planned?” his voice faltered and for once, you saw the vulnerability in his expression. Diavolo was  _ lonely _ . Despite all he owned, he was feeling left out of gatherings. There was a hint of desperation in his voice as if he had put all his eggs into one basket, hoping to be included in this activity. 

His expression was everything Simeon had hoped for. Diavolo had walked into every trap he and Lucifer set up for this very moment. The pleading expression and the puppy dog eyes he was giving Simeon were just a bonus. The angel’s face broke out in a wide grin while he regarded the redhead. “Well, since you asked so nicely, it’d be rude of me to not let you join us. It’d be a good surprise for Lucifer to come back to, yes?” 

Diavolo’s face brightened instantly. He nearly leapt up from his seat in excitement. The tension in the room broke instantly once he heard he was to be included in your rendezvous for the week. “Oh how great! I’ll make sure my evening is free! Bar--” 

Simeon silenced Diavolo with a simple gesture, holding his hand up to stop the demon prince from going too ahead of himself. “But first….” The pitch of Simeon’s voice dropped an octave. He stood up, sauntering to Diavolo and gazed deep into his eyes. “To land a role in any film, a proper audition is needed, yes?” 

“Ye-yes…” Diavolo stuttered, looking down at the angel who was mere inches from his face, the smile told millions of secrets that he had only begun to unravel. In his flustered state, he didn’t even notice Simeon’s subtle movements until something was pressed into his hand. Diavolo didn’t need to look down to know what it was. The weight and the shape in his palm told him all he needed to know.    
  
Simeon retreated, satisfied once recognition flitted across Diavolo’s face. “Well, I’ll see you later tonight! I have to help tutor Luke a bit and prepare some snacks for the movie. See you!” He waved and made his way to the door. As he passed you, he slipped something into your hand. 

“Prep him well, will you? He’ll need all the help he can get.” 

You waited until after the door clicked shut to look down and have your suspicions confirmed. A little remote, no doubt one that was connected to the thing Diavolo had in his hand. 

There was a long gap of silence, one which made the tension grow once again. The two of you stared at each other for what felt like hours and you sat there frozen in your seat. Who would make the first move? Who would speak first? Would Diavolo even consider submitting himself to such humiliation? Surely he wouldn’t?    
  
“Well…” He cleared his throat, his blush turning his cheeks as red as his hair. “Think you can help me with this?” 

There was a certain charm to the way he was so sheepish and how he hesitated with his words. It made you want to take care of him, take charge and promise him everything would be all right in the end. “Of course.” You replied smoothly, pushing the shakiness out of your voice as you took control. Simeon  _ did  _ task you with ensuring his proper preparation, the last thing you wanted to do was disappoint the angel. 

You strode over to where he was and slipped the control into your pocket for the time being. You gently guided him to bend over the arm of the chair he was just sitting in. “Relax.” you reassured. “I’m sure you’ll do just fine.” 

You kicked his legs apart, making sure his knees were bent to prevent him from passing out.Your hand caressed the swell of his ass and he shivered under your touch. The smallest traces of a moan left his lips and he quickly buried his face into the cushions to hide from the shame. You hadn’t even done anything to him and he was already trembling. “Are you excited?” You asked, tracing the cleft of his ass, trailing your finger up and down the seam of his pants while you waited for an answer. You noticed the crotch area was already rather tight and you couldn’t help but smirk, realizing how affected he was by the simple gesture of being invited to movie night. 

“I… I’m a little nervous.” he admitted, stuttering. The normal confidence he had around others was all but gone as he submitted himself to your touches and your approval. “I don’t… I don’t want to disappoint.” 

“You could never disappoint.” You cooed, reaching around to undo his pants. “Just remember to breathe.” Your hand dipped between his legs to grasp his half hard cock, earning you a loud gasp. His dick twitched in your hand as you felt just how large he was. Even without being fully erect, he was a girthy monster, your hand was barely able to circle around his shaft and your walls clenched at the thought of possibly taking him in later that night. 

“There now, see? Just like that, be good and show me how excited you are for tonight.” You encouraged, stroking his length and watching his body language change from nervous to lustful. You slid his pants down his thighs to gain better access to his cock. Looking down and seeing his member hanging hot and heavy between his legs was such an enticing sight. His balls pulsed with need, nearly ready to release his load prematurely if you kept teasing him. 

“My, my, you’re quite hard already, aren’t you? I know you’re going to be perfect for the audition tonight.” You praised, letting go of his cock to palm the smooth, soft swell of his ass. He whined, once again burying his face into the cushions, ashamed at how turned on he was from just the thought of later activities and your teasing touches. 

Diavolo shivered, unable to process much outside of the fact that his precious exchange student was currently making him feel a certain way he couldn’t quite comprehend. It felt _good_ to be the center of attention. It felt _good_ to be under you, at your mercy and letting you take the lead. It only made him anticipate the activities to come. “I’ll… I’ll do my best to impress.”  
  
“Oh, I’m sure you will.” You smiled softly and plucked the plug from his hand. Even if Simeon and Lucifer had left you out of planning to get Diavolo involved with your movie nights, you were rather satisfied with the outcome to say the least. You assessed the plug and had to admire Simeon’s taste. It was slim, long and textured in a way you imagined would tease the demon prince for hours but not enough to make him cum.   
  
You traced Diavolo’s ass crack with the tip of the toy, paying close attention to his body language and memorizing the moment you had the demon prince himself bent over and at your beck and call. “Well now… this wouldn’t be very good to go in dry…” You mused before you sauntered around him and placed the toy at his lips. “Make sure it’s nice and wet, won’t you? You wouldn’t want to get hurt taking this all in, now would you?”   
  
He looked up at you, his golden eyes filled with a fair amount of lust in them before he dutifully took the toy into his mouth, obediently licking and sucking it until it was coated with his saliva. You could see how much it hurt his pride to do such a debauched thing based on how hard he was gripping the cushion below him, but his hard cock told you how much it also turned him on. He couldn’t even hold back a moan when the plug hit the back of his throat as you pushed it in further, ensuring he got every inch of it coated. “Good boy….” You praised, patting his hair softly and admiring how pretty he was whenever he blushed.   
  
Once you deemed it adequately lubed up, you went back to his waiting ass and pressed the toy into that tight hole of his. You heard him gasp at the sudden intrusion before his whole body seemed to relax and he let out a breathy groan. In no time, he was pressing _himself_ against the toy, willing it to go deeper and deeper into him. He was eagerly moaning at this point, cum beaded at the tip of his cock as he was finally getting the attention he craved.   
  
“Aww look at that, it went all the way in so fast.” You praised, giving his ass a quick pat before pressing the toy into him as far as it would go. He rewarded you with a particularly lewd moan when the tip of the plug brushed against his prostate and made him see stars. “You were waiting for something like this, weren’t you?”   
  
“I… I maybe…” he mumbled, his words were muffled by the cushions. It was adorable. He was so eager to join in on the fun. You could tell just how lonely he was and how jealous he had been when he found out Lucifer was having these movie nights without him. It almost made you forgive Lucifer for showing him the movie you made. _Almost._   
  
You giggled once everything was in place. Getting his pants back on was no easy feat considering how hard he was, but there were still a few more hours before you were supposed to meet back up with Simeon. Not to mention, he had quite the mountain of paperwork to do still. “There you go, all nice and tidy.” You announced once he wearily buckled his belt again. The bulge in his pants looked almost painful and you resisted the urge to reach out and fondle him.   
  
Instead, your hand went to your pocket and you clicked the power button. The reaction was almost instantaneous as Diavolo doubled over, collapsed onto his knees and his whole body trembled when the toy buzzed to life. His soft, breathy moans couldn’t cover up the hum of the toy in his pants and his embarrassment was only intensified by this fact. His cock throbbed in his pants, yearning for freedom once again, but he had duties to attend to even if his mind was far removed from them. Possibly the most arousing part was how attentive you were, how much care you showed him as you toyed with his body. That, was the most erotic part of it all. He had lost all power over you and now, you controlled him at the touch of a button.   
  
You watched writhe a bit longer, admiring how his body contorted as he tried to find more stimulation somehow without begging for it. After a while, you lowered the intensity of the toy until it just barely vibrated at regular intervals just enough to remind him who was in charge. “I’m sure you have so much work to do before we get to meet up with Simeon again.” You said, acting as if nothing was wrong at all. “I actually have a report I need to work on too. Do you mind if I stay here and ask you questions?”  
  
“N-no.. not at all.” Diavolo managed to stutter out. It took all his strength to stand back up, when he did manage to get back on his feet, he felt light headed, his mind was solely focused on pleasure and not anything else he had to get done.   
  
However, with you pulling out your books and settling down at the table to get to work, he made his way back on shaky legs to his desk where his mountain of documents awaited him. Diavolo yearned to touch himself while his lower half was hidden by his desk. It would have been perfect for him to just get a little bit of relief from the torment you had wrought up on him. However, he knew better than that. He knew if he could be patient, there would be a much greater reward than the immediate relief he sought. 

It was just unfortunate that he would have to suffer for hours to get to his goal. And as he finally settled down to start going over contracts with neighboring lands, the toy inside of him hummed to life once again, sending jolts of pleasure through his body until he couldn’t see straight. Just as he felt like he was about to pass out from being denied the ability to cum, the vibrations stopped and he was left on edge. Breathlessly, he would glance over to you diligently working on your report, the perfect image of innocence before him even though he knew that in your palm, you held the incarnation of sin itself. 

It would be a  _ very _ long afternoon indeed for him. 

~~

Diavolo wasn’t wearing a leash, but he might as well have been with how eagerly he followed after you down the long hallways and to your usual meeting room where Simeon awaited you two. The promise of snacks wasn’t a lie as the scent of popcorn and cookies got stronger the closer you got to the room. You threw the door open and grinned widely when you arrived. “We’re here!” You announced with Diavolo in tow. 

The lights were already dimmed and a rather familiar film was playing on the screen. You blushed madly when you were faced with the movie you had made earlier with Lucifer and Simeon. Diavolo seemed to be absolutely entranced with the images flashing across the screen. There was an unabashed adoration that flickered across his face and a yearning you couldn’t quite place in his expression while he watched the lewd acts play out. 

“And you’re  _ late. _ ” Simeon chided, his gaze was hard and cold. “Not a very good start to the auditioning process, now is it?” His voice cut through whatever daydream Diavolo was in and the demon prince stood up straight in attention.    
  
_ Ah, he’s in one of those moods… _ You smiled sheepishly, ushering Diavolo in and shutting the door behind you. “I’m sorry, I got wrapped up in finishing my latest report so that the rest of the weekend is free.” You explained, hoping for some mercy; though you knew it likely wasn’t going to happen. 

He ignored your excuses and busied himself with setting up the camera. Simeon took one long look at Diavolo, his expression was unamused and he almost seemed bored. The angel finished fidgeting with the camera before turning to Diavolo. “I have high expectations for you. I’m hoping for a rather riveting performance.” He had the smallest of smiles on his face before gesturing to the bed. “Why don’t you start by showing me how well you can undress yourself.”    
  
Simeon took a seat in the corner of the room, crossing his legs and leaned against the armrest of the chair. His gaze never left Diavolo as the prince sheepishly climbed onto bed and started to undo the layers he had on. You moved to help him but Simeon stopped you, beckoning you over to sit on his lap while Diavolo did his thing. 

“Come now, the view from here is so much nicer, isn’t it?” 

You nodded dumbly, not able to resist Simeon. The sound of your moans coming from the television had you remembering exactly what he had done for you just a few weeks prior and you squirmed in his lap. 

“I hope you’re looking forward to this.” The angel murmured. “It’s not every day that we are graced with the presence of Lord Diavolo himself. We should make the most of this, yes.” He smiled sweetly, grasping your breasts while he trained your gaze back at Diavolo who was in nothing but his boxers. There was a noticeable wet spot at his crotch and his hard cock strained against the soiled fabric. Even in the dark, you could clearly see the outline of it and once again, imagining what it might be like to take him. 

Just as Diavolo started to peel off his boxers, Simeon stopped him with a quick gesture of his hand. The redhead audibly whined. He was so close to being  _ free. _ Yet, he knew better to disobey if he wanted to impress his audience. He couldn’t help himself from stealing glances at the screen. Watching you get fucked by both a demon and an angel had him wondering just how tight you would feel beside Simeon and he hoped to experience that later that night. He licked his lips, barely aware of Simeon getting up and getting a hank of rope from one of the drawers. It wasn’t until he felt the weight of the rope on his shoulder did he realize something was happening. 

“Distracted are we?” Simeon teased, covering up the screen just as the film behind him reached its final climax. The sounds of shouting and moaning echoed in the room and Diavolo blushed at just the thought of what that scene looked like. However, he had more pressing concerns to worry about in front of him. Simeon looked like the very definition of sin in that skin tight get up he wore regularly. There was a reason why he didn’t enforce the school uniform rule on the angel. The eye candy was much too tempting for him to resist. 

Simeon’s fingers were deft, gracefully working Diavolo’s arms behind him and securing them in place with intricate knots. “There we go. Now, you can focus much better, yes?”    
  
Diavolo nodded, his eyes now solely entranced and fixated on Simeon. “Yes… sir.”    
  
There was a genuine smile when Diavolo let the title slip from his lips. “Oh… I like how that sounds coming from you. Call me that again when you cum.” The angel swooped in, kissing the demon prince deeply, pushing him onto his back and settling between his legs. He beckoned you to come over as well to join them. Once you joined him between Diavolo’s legs, Simeon finally started to take off the last piece of clothing he had on. 

“My, my. What a mess he made.” He commented, noting the large stain on the boxers before tossing it to the side. “Did you have fun this afternoon?”    
  
You nodded, holding up the remote to the toy still inside of the man below you and pressed the button to put the vibrator on the highest setting. “I sure did!” You giggled while Diavolo screamed, writhing from the stimulation. Simeon ignored him, his attention affixed to you and his eyes were filled with pride and adoration. He stroked your hair before kissing you as Diavolo watched helplessly. When the kiss broke, you were breathless and more than ready to entertain whatever whim Simeon had. 

“Now… what shall I do with you... “ Simeon finally turned to Diavolo and casually stroked the man’s length, making him squirm even more. The buzzing in his ass slowed and eventually stopped, giving him some reprieve. “Aww, the batteries must have died.” Simeon pouted. “No matter, It’s time we gave our … pet a new toy, yes?”    
  
“Sounds like a plan.” you agreed, reaching between Diavolo’s legs to slowly pull the plug out while Simeon continued to tease his dripping cock. “What did you have in mind?” 

“Come with me, Let’s go looking together.” He suggested, leaving Diavolo right at the edge of a climax. “The night is still young, my prince. There’s so much fun to be had.” 

Diavolo was left in silence as Simeon led you away to a corner of the room he could not see from his place on the bed. HIs mind raced with the possibilities of what was to come and it only made his dick twitch in anticipation. A small puddle of cum pooled on his abdomen as his cock continued to leak and when Simeon came back to see the mess, he could only tsk at how poorly Diavolo was misbehaving.    
  
“My, my…” He chided, smearing the fluids across Diavolo’s abdomen. “This just won’t do.” He shook his head, feigning disappointment before selecting a cock ring and securing it around the base of his shaft. Diavolo hissed at the feeling of being so restricted after just having a taste of freedom. “There….” Simeon smiled, patting his member. “Now we can have all the fun we want without worrying that you’ll cum too soon.” His expression was so sweet, it almost made Diavolo sick, but he didn’t have much time to dwell on that fact.    
  
Part of playing with him meant you and Simeon dressed him up in the prettiest toys you had. Nipple clamps with bright red jewels were affixed to his chest. A delicate chain connected them and that was soon attached to the collar you placed around his neck. “A proper leash for a proper pet.” You explained, patting his cheek softly. His heart melted seeing you so content. Your touches sent him right into bliss. The pain at his chest felt negligible when he was able to bask in the attention he was getting.    
  
It had been so long since he had been pampered in such a way. He had  _ missed  _ those intimate touches, those longing looks. He craved being coddled and here you and Simeon were, giving everything he could dream of. Though he was barred from entering heaven, he wanted to believe that what he was experiencing in that very moment was akin to paradise. Diavolo struggled against his bindings, wanting to return the favor, he wanted to thank the two of you for showing him what it felt like to be adored. He whined, putting on the most impressive pout he could muster. “Please… I want to touch…”    
  
Simeon paused in the middle of undressing you and scoffed at the request. “A little early for begging, isn’t it?” He mused before completing his task. “Our pet’s a little talkative, why don’t you shut him up while I do a little disciplining?”    
  
You nodded, crawling up Diavolo’s side and straddled his face. You pat his head once more before lowering yourself over his lips. “Keep me entertained, why don’t you? I promise if you do a good job I’ll sit on that fat cock of yours.” You didn’t give him time to reply before grinding yourself down onto his face and letting his tongue do the work. 

Simeon smirked, parting Diavolo’s legs so he could properly situate himself between them. He could spend hours watching you ride the prince’s face if only he didn’t have more important things to do. The angel waited for you to get a hold of the headboard to keep yourself stable while grinding down on Diavolo’s face in between breaths. From the sounds of your moans and your breathy sighs, it seemed as though the prince had quite the talented tongue. Simeon wondered briefly what it would feel like if he was in your position before he steered his focus back to what was right in front of him.    
  
Having prepped Diavolo earlier meant that the toy he had chosen slid in with little resistance. In fact, it was as if the thick dildo was being sucked into the prince’s hole with how easily it went in. “My, oh my….” Simeon mused, impressed with how quickly Diavolo seemed to adjust to taking the toy. “We really do have to teach you patience, don’t we?”    
  
Simeon started a sinfully slow pace, fucking Diavolo with the toy and simply taking the time to admire every reaction he was able to pull out of the man below him. His moans were muffled but there was no denying the pleasure he was getting out of this. It only made it more sweet to torment him and deny him his climax. 

Time and time again, he would pull the toy almost all the way out before inching it back inside. Even with the cock ring on, Diavolo’s member throbbed and his seed dribbled from the tip. Simeon made sure to tease the rest of the demon’s body, tugging at the chains to the nipple clamps, placing soft kisses all along his thighs and pelvis but pointedly ignoring the aching cock that begged for attention. He loved seeing Diavolo’s muscles tighten anytime he was close to getting what he craved and only drove him to tease the man below him right to his breaking point. 

He counted the times you came on top of Diavolo and decided that maybe after your second orgasm you could rest a while before he finally ramped the pace up. “Rest a bit and watch,” Simeon gently guided your tired body to where he sat, letting you sidle up against him in content while he continued his work. He worked in a methodical, almost calloused way when it came to controlling every aspect of Diavolo’s pleasure that evening. It was equal parts arousing, amazing and terrifying to you just what Simeon was capable of.    
  
Diavolo gasped for air once you were no longer on top of him. He stared at the ceiling, not sure what he should do next. The taste of your essence lingered on his lips. He was sure he could have continued until he either passed out from lack of oxygen or you did from overstimulation. Unfortunately, that scenario would only remain being a dream and he could only daydream about it. He was instantly snapped back to reality when Simeon roughly shoved the dildo that had only been teasing him all the way in without warning. 

The prince let out a choked cry, his whole body tensing in the sudden roughness. He loved it, he loved every second of the sweet torture the two of you had come up with. He couldn’t tell when the pleasure stopped and the pain began, but he didn’t care. He wanted more of it, he craved the attention and would do anything to be on the receiving end of it. Glancing down between his legs, his heart skipped a beat when he saw how happy and content you were snuggled up against Simeon who was relentlessly fucking him. There was a tenderness in your expression that he wished you would direct his way. 

“Look at you… So sensitive.” Simeon cooed, tugging at the chains attached to Diavolo’s sensitive nipples. “I’ll bet you could have just cum without me touching your cock at all. You’re that much of a needy slut,, aren’t you?” He chuckled, slamming the toy inside of the prince once again. 

“Y.. Yes…” Diavolo sputtered arching into the thrust, wishing that the toy would go deeper, stretch him wider, do  _ something _ to tip him over the edge. “I… I need…” 

“You  _ need? _ ” Simeon repeated. “We’ll have to teach you some lessons, now. Good pets don’t  _ need  _ anything. They  _ beg _ for what they want.” 

“I… I ahhh~~” Diavolo’s brain short circuited when you had grabbed a nearby vibrator and pressed it against the tip of his cock. Whatever he wanted to say promptly flew out the window as he was thrown into a world of bliss. “I… I…”    
  
“Use your words.” You encouraged, turning the vibrator on higher. “I can’t understand what you’re saying.” 

He wanted to  _ fuck. _ He wanted to  _ be fucked. _ He wanted everything all at once but he couldn’t express it with how overloaded his senses were. “I … I want to…” 

“Go on.” 

“I want to fuck… I want to fuck you and cum…  _ please. _ I want to cum so bad. I did good, right? You weren’t bored right? I can keep being good, just let me cum, please, please  _ please.  _ I’ll be the best slut you’ve ever seen.” 

You looked up at Simeon, wondering if the angel approved of Diavolo’s groveling. His expression betrayed none of his emotions and he simply pressed the toy further into Diavolo’s ass, garnering a loud, appreciative moan from the man beneath him. “Very bold words… I hope you’re ready to live up to them…” He said quietly. 

“Yes, yes. I promise I will! I’ll do so good. I’m a slut, a fuck toy for your entertainment. I’ll do anything for you. Please, just… I want to cum so bad. Can I please?” 

“Hmmm” Simeon hummed softly, carefully considering Diavolo’s words. “Yes, you may.” 

Diavolo gasped, his heart nearly beating out of his chest when he received permission. However, his excitement soon grew into dismay when Simeon produced a long length of ribbon to tie the vibrator against his cock. “Wh.. wait, you said I could cum…” He whined.    
  
“I said you may, I did not say when.” Simeon stated smoothly. He reinforced his statement by turning the toy onto its highest setting before he pulled you into his lap. The angel had your back towards him and he spread your thighs out to let Diavolo see just how drenched you were. Simeon reached between your legs and spread your lower lips, toying with your clit and making you moan in need. He wasn’t ready to reward his new pet just yet. 

What he was ready for was making Diavolo watch you getting fucked. There wasn’t enough desperation yet, not enough hopeless need coming from the prince. “Is this what you want?” Simeon asked, grunting as he was balls deep inside of you. “Is this what you want to feel? How hot they are? How tight they’re going to be around your cock?”    
  
The pace he set was hard and fast. You had craved being filled after being eaten out so thoroughly before and Simeon’s cock was filling every craving you had. You ground your hips down to meet every one of his thrusts, loudly moaning every time his cock hit the most sensitive spots inside of you. It wouldn’t be long before you would be climaxing around him and he knew it. As soon as he felt your walls fluttering around him, he slowed his pace and let your racing heart calm down just enough to leave you hanging. 

You whined squirming in Simeonn’s lap, hoping he’d keep going, but he stayed still and observed Diavolo’s expression instead. You followed his gaze and you were met with the most delightful visage of the debauched prince, blushing and desperate for attention. Tears were freely flowing from his eyes as he babbled incoherently, begging to experience the same thing he was witnessing. 

“Please… sir, I want to cum” His voice cracked. “May I now please cum?”    
  
“What do you think? Do you think he’s deserved it?” 

You pretended to ponder over your answer, dragging out Diavolo’s torture for a few moments more. “I think he’s done well enough to be rewarded.” 

  
“Hmm, I think so too.” Simeon agreed. 

He was loathed to leave the warmth of your pussy as he laid you down on the bed; but he was sure his cock would be satisfied soon enough in other ways. The toys were taken away, the cock ring removed and Simeon waited a moment for Diavolo to get his wits about him before offering your body up. “Well, go on. You’ve earned it.”    
  


Even with his arms still bound behind him, he was able to roll onto his sides and bring himself onto his knees. It was rather impressive, to say the least how quickly he got between your legs and plunged himself into your waiting hole. Though Simeon’s cock had stretched you out earlier, nothing compared to how  _ full _ you felt once Diavolo was sheathed within you. You wanted to savor the moment, but there was no time to think as he started to pound you with his cock. 

It was your turn to be a blubbering mess. The fullness, the roughness, the wanton need that oozed out of his very being was intoxicating and you were lost in the pleasure of it all. “Oh,  _ good boy _ .” you praised, reaching up and pulling on his hair to encourage him to keep going. “What a good slut you are.”    
  
Hearing your praise only made him go feral with need and he redoubled his efforts to gain more of your compliments. Diavolo was so lost in the moment, he nearly forgot Simeon was there until he felt something warm press up against his ass hole. His pace stuttered and he looked back in confusion. That bit of disobedience was met with a hard slap across his ass cheek. “No one said you could stop.” Simeon hissed, pressing himself into Diavolo. 

“Prove to me how good of a slut you are and make us cum at the same time.” He demanded. 

This was it. His final test. He put everything he had into turning himself into the perfect pet, the ideal fuck toy for the two of you. Diavolo resumed his pace inside of you, making his strokes long and hard while his ass clenched around Simeon’s cock to ensure the man behind him was enjoying the hot tightness there. His own pleasure didn’t matter to him anymore, it was pleasure in itself to serve the two of you. 

Euphoria was reached when he was the best slut in your eyes. 

Diavolo did as he was promised, making both you and Simeon climax at the same time. You were the first to crumble. Your inner walls clenched around his cock, sucking him in deeper, milking him. All the while, Simeon’s thrusts became erratic as he reached his climax and spilled his seed deep into the demon prince. The moans coming from his lips were the most delightful symphony. 

“Go on, show us how pretty you are when you cum.” 

Finally having the permission to climax, Diavolo slammed himself into you, burying himself as deep as he could go before releasing his load into you. The hot spurts of his seed filled you and you swore you came again just from that feeling alone. The groan that came from the back of his throat sounded more like a possessive growl to you and the heat behind his golden eyes was practically palpable. 

It took a long moment for the three of you to come down from the high of such an intense climax. Simeon was the first to recover. He carefully extracted himself from Diavolo and went about finding some towels to help clean up the worst of the mess you had all made. Along with that came the snacks he had baked earlier and water. Setting everything aside, he finally freed Diavolo’s arms and the demon prince visibly slouched in relief as his aching muscles finally got a chance to relax. 

He wasn’t ready to leave the warm confines of your pussy just yet and shifted himself to cradle you against his chest while Simeon fed you cookies and made you sip some water. Diavolo’s fingers brushed your tousled hair and you stared at you with nothing but admiration in his eyes. “So, do you think I’d get a callback after that audition?” 

Simeon chuckled softly, sliding back into bed with a bowl of popcorn and offered some water to the prince who gulped it down eagerly. “Absolutely. You’re the perfect fit for the role.” 


End file.
